My Boyfriend Was Cheated On and Has Trouble Trusting Women. What Should I Do?

girlfriend confronting cheating boyfriend

I have been dating a guy I met online for about 3 months now. He has been divorced for 16 years. I have never been married. He’s 42, and I am 40. Unfortunately, his ex-wife cheated on him, and married her lover the day after their divorce was final. My boyfriend seems to be VERY obsessed with never allowing anything like that to happen to him again, and is easily upset by any talk of men I dated before him, even though all of those relationships were extremely superficial and I maintain absolutely no contact whatsoever with any man I ever dated before him. My boyfriend has many good qualities, and I really like him a lot (I’m starting to love him). I just wanted to know, in a general way, what does it take for a man to get over being cheated on by an ex-wife, particularly if it has been many years now, and he still seems to be putting up walls? Most of the information I have found on the internet dealing with divorced men pertains to issues surrounding the recently divorced, and most of the information about cheating has to do with divorced men who cheat, not men who were the cheatees rather than the cheaters. Do you have any general advice for a (never married) woman dating a long-divorced man who has trust issues going back 16 years to an unfaithful first wife? I REALLY want my relationship with him to work out. What should I do?


If you were ever cheated upon, what would your partner have to do to convince you that he’s safe?

Dear Vicki,

Great question. Straightforward answer. All you have to do is look at it from another angle.

If you were ever cheated upon, what would your partner have to do to convince you that he’s safe?

In a lot of circumstances, there’s not much someone can do explicitly to instill trust. I think back to a girlfriend of mine who had a boyfriend who was polyamorous. This arrangement pretty much meant that he openly cheated on her while she remained faithful to him, hoping that he’d change. She was free to do the same, except she didn’t want to. This experience scarred her and all of her trust issues came to surface when she started dating a very flirty burgeoning dating coach. She could never believe that a man like me who appreciated other women wouldn’t cheat on her, and she broke up with me (about three times, to be exact.)

I only share that story as an example of how you can have your heart in the right place, but still not do anything to assuage someone with deep seated issues.

On the other hand, my wife was cheated on by her ex-husband and other long-term ex-boyfriends. How she managed to trust me, even when she found a pair of panties in our new hamper after a business trip, is beyond me. But the main reason, I’m guessing, is that I haven’t given her any reasons to doubt my integrity.

And ultimately, Vicki, that’s really all you can do. You can’t erase his past, his hurt, or his shame. All you can do is make him feel safe and loved and lucky.

You can’t erase his past, his hurt, or his shame. All you can do is make him feel safe and loved and lucky.

He may never “get over” the experience of having blind faith in a partner; I know my wife hasn’t. But, if he’s emotionally available — and thereby, a suitable partner — he’ll realize that you have nothing to do with his ex-wife. To keep you at bay because of an awful mistake made by another woman 16 years ago, would effectively mean the end of your relationship. He’s gotta let you in.

The woman who let me in, despite her trust issues, became my wife. The woman who didn’t is just another ex. Which is just a longwinded way of saying: do your best, but it’s not really up to you.

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  1. 1
    Curly Girl

    Really want to hear the panties in the hamper explanation! 🙂

    1. 1.1

      Me too!!   Just more bs

      1. 1.1.1

        Patty and Curly Girl:

        Patty, do you mean the “panties in the hamper” story is bs? If so, unless you think Evan is totally lying in his post about what happened, it’s true. I pulled it up immediately by Googling “panties in the hamper evan marc katz.” In other words, it’s not that hard to find the first-person source, even if he doesn’t reply directly to you here:

        Of course, if you think Evan is generally bs’ing, there’s nothing more to say. Personally, his advice has totally and positively transformed my dating life and prospects for finding lasting love, which is my goal.

        1. Persephone

          The panties-in-the-hamper story is amazing. She put herself on a limb to trust Evan. The wife had so much to lose if she had chosen not to trust his answer. She chose to have faith in her husband. If he had finally fessed up, having been guilty of adultery, the outcome would have been better by letting him voluntarily come forward. They might possibly have been able to repair things, had he genuinely been guilty. If the wife had accused him simply based on the panties, with Evan being innocent, they would have never been able to repair the relationship. It was turned around to become an even stronger bond because of her faith in Evan. Again, an amazing story.

  2. 2


    Your boyfriend needs professional help. It has been 16 years.

    Trusting another person is ALWAYS a leap of faith. There are no guarantees. If he wants a certain kind of happiness he has to be vulnerable to risk. That is the bottom line. Either he accepts it or he doesn’t.

    1. 2.1

      Its not really how it works…..ive been cheated on..i am in fact a male and i have a hard time trusting my partner when she leaves for extended amounts of time. At times he may seem a bit clingy, but thats not really it, hes giving himself the mental state of mind knowing where you are and that your not betraying him, my partner put an app called life 360 on my phone, and for me. At lease when i fear she may be cheating on me I can check where she is to confirm to myself that she couldnt be cheating on me there. For instance a visit to an animal shelter or something unusual would feel more suspicious to someone like myself rather than say one like you who has never experienced the pain of being cheated on. My x cheated with 3 men before the relationship ended, its not trust in you that needs to be built up, its trust in trusting you…its hard to explain, im sure he trusts you but he needs to trust your relationship more.

  3. 3

    I think a dynamic of having to “prove” yourself is really, really harmful, because you can never prove it and you’ll just be trying forever. You may be able to deal with it now, but what if it never changes? Can you live with this person for the rest of your life knowing that he will never believe in you?

  4. 4

    I had a similar experience in a past relationship. I kept reminding him I wasn’t his x and that I didn’t cheat on my x. In the months we dated he knew he could trust me. But his being hurt so deeply he says he’ll never again marry or build a life with another. He is happy with the girlfriend he has now, and plans on it staying just a girlfriend/boyfriend. I wonder if she knows that?
    Anyway, after 16 years he is not going to change the way he feels. I’d move on. I know that is easier said than done. But when they can’t forget the past…you can’t have a future.

    1. 4.1

      I just got dumped by a divorced man of 3yrs, she cheated on him. He’s so damage from it, got the idea in his head to never be in a relationship, but casual and uncommitted is okay. Well he met me and with me for the last 11 months,   swear he loves me more than anything, but so scared,   he ran. And we can’t even be friends because he would want me too much and loves me is what he doesn’t want to feel. So he hook up with someone to convince his logic plan.

      1. 4.1.1
        Karmic Equation

        My current bf was cheated on by previous gfs. His last gf may not only have cheated on him (he didn’t catch this one red handed so to speak) — but she put him through the wringer with lies at the end of their relationship.

        Yet he still trusts me and committed to me.

        I believe men — and women — who use past relationships to justify their inability to commit or to trust in current relationships aren’t ready for relationships. They don’t want to be alone. But they don’t want to “work” at relationships either. They want to coast along with pseudo relationships.

        And there’s nothing wrong with a divorced man or woman never wanting to remarry. It’s only wrong if they know the person they’re with wants to eventually marry and s/he doesn’t let his/her partner know this up front. If the partner remains in the relationship after such a revelation, then the partner is implicitly accepting that there will never be more.

        If a woman wants more than just a bf/gf relationship, as soon as the man says “I’m never remarrying again” — she needs to believe him. And exit the relationship if that is counter to her long-term goals. He’s not stringing her along if he tells her and she doesn’t listen to him.

        1. Christina

          Bingo  Karmic Equation, just got out of a relationship with a person who was cheated on, 10 plus years ago. I went out of my way to give assurance and security even when I sense distance and self-protectiveness. All the right things will be said and all the actions would contradict.  

          After a couple of months of being together, I brought it up. The response I get is privacy is important, generally not so expressive, the cheating episode and lack of self-esteem, need reassurance.

          Even told me I was too emotional and how it was too much. No comfort was offered. So OK, I decided to learn how to self-soothe and rely on myself emotionally. I started to be like him, something I didn’t like. I enjoy being in touch with my emotions, trusting, open and true to myself. I started asking myself hey, why is it that even when I am unhappy, responsibility was shoved into my face when it wasn’t my issue to begin with.  

          It makes me sick that someone would prey on my empathy to justify bad behaviour. I soon found out there were messages to multiple people via a dating site, from the beginning of the relationship until now. With messages like “I find you interesting, this is my no.” Also a hidden vacation with the ex. The same ex who is also the housemate. Also a series of lies along the way.

          I myself have been upfront and honest. Even to the extent of not chatting with platonic friends.

          So your comments kicked in

          “I believe men – and women – who use past relationships to justify their inability to commit or to trust in current relationships aren’t ready for relationships. They don’t want to be alone. But they don’t want to “work” at relationships either. They want to coast along with pseudo relationships.”

          So true. Keep at arm’s length, reluctant or refuse to address matters.



  5. 5


    Very good points made above. At some point, you will be drained and maybe even resentful from constantly having to prove yourself. I would tell him that if your relationship is that important, then he needs to get the help necessary to resolve his issues. You cannot fix this. You can love him and support him in his efforts to grow and get on the other side of it, but you can’t fix it for him.

  6. 6

    I think some men are a lot more emotionally fragile then the mass media would lead people to believe. They don’t have the emotional fluidity of women, if they’ve been cheated on by someone they had ‘blind faith’ in, they could be utterly destroyed and broken by the experience. However, it’s been 16 years, and since he’s now in a serious relationship with you, it’s probably apparent to him that living in a shell for the rest of his life isn’t the way to go. If he’s with you, then a significant part of him really wants to heal and open up to another person. I think the solution is to point out to him that both he and his ex-wife might have been more naive in their twenties. If the current age has taught us anything, it’s that women, as well as men, can cheat. But some people will not cheat, because they’ve made the decision not to and have the character to support that determination. Notice it’s not they won’t cheat because they might never be tempted, or that they can’t, but that they won’t. Since you are both in your 40’s, both of you should have the maturity and strength to correctly assess such other’s integrity as human beings.

    I don’t think having ‘blind faith’ in his wife was necessarily a good thing. Sometimes men relegate women to some sort of support role and forget to relate to them as genuine people. Like she existed only as an idea of his wife, rather than the person she really was. I believe in a marriage, feeling lonely and not understood, is a lot crueler feeling than feeling lonely as a single person. As a spouse, it’s not your job to turn a blind eye to such things, because they will happen, but instead to offer a genuine effort to support and understand another person when it happens. Yes, they are your spouse, but they are still themselves as well. Sometimes the other party can seem very unlovable to you, being in a committed relationship means that nevertheless, you should try to be compassionate and loving.

    Maybe in the previous relationship, he never really paid enough mind to her, and just assumed she was happy . Without emotional understanding, that’s not much of a marriage.

    You need to teach him how to pay actual attention to the progress of the real relationship. If the emotional content of the current relationship is more understanding and genuine than his previous marriage, he will gradually grow to trust you because he’ll grow to trust his own emotional understanding of the relationship. I think you need to be patient and strong if you want this relationship to work. But he needs to be told that he needs to grow up as well, to put the past behind him, and to forgive his wife and well as recognize that his younger self is not the man he is now.
    It’s going to be difficult, but for crying-out-loud, he’s in his forties. Tell him it’s his last chance not to die alone, being lonely and a coward.

    1. 6.1

      That was an excellent post until the end. Demeaning the guy and calling him a coward will in no way help the situation.

    2. 6.2
      A random 40 year old single guy

      Men have been shamed their entire lives, often by their own mothers.   The best case scenario is once he hears “coward” he’s going to pretend she didn’t say anything at all.   Appeal to his masculinity: remind him that he has to make a choice and stick to it.

  7. 7

    @ #4

    A great nugget:

    ” But when they can’t forget the past you can’t have a future.”

    1. 7.1
      James Malone

      Awesome saying!

    2. 7.2
      A random 40 year old single guy

      Yup, a man needs to transform his very DNA sometimes.

  8. 8

    My boyfriend of over a year was cheated on by his ex-wife — he was a workaholic, she felt neglected and the bloom had worn off…nothing original. Add to that a few previous girlfriends who had stepped out on him, and (most disturbing to me, and almost a dealbreaker) a relationship with a married woman. Guess who has trust issues now.
    He puts up a good front of not worrying about it, but the jokes about how I’d leave him for some fancy co-worker come out occasionally. Or if we got married, and he was inattentive, I’d step out on him.
    And then about a month ago he appologized that I have to deal with the results, that he really doesn’t trust women. My first response was that everyone has baggage, including me.
    But, after thinking about it, and processing it, I’ve realized that I’m great enough for him to get over it, gosh darn it! And if he can’t, then I’m just gonna have to move on. I’m not saying next week, or even next month…but at somepoint, if I’m not content with the way things are going, what’s the point in continuing. He doesn’t know this, I may tell him the first half, but the second sounds like an ultimatum when it’s not. It’s just being realistic.

    1. 8.1
      A random 40 year old single guy

      Jokes about leaving him are certainly dangerous territory.   The trouble with invoking thoughts like this is that they have an annoying tendency of becoming self-fulfilling prophesies.

      I used to be quite a joker in my younger years and I’ve decided I’m tired of inadvertently stepping on others’ weak points.

  9. 9
    Mikko Kemppe - Relationship Coach

    What a great and interesting topic. I agree with Evan that this is a very tricky situation and in reality there is really not much you can do except to love him and accept him as he is.

    I have been cheated before and for me personally it helped when I realized how I also contributed to “driving” my girlfriend to cheat. By learning to forgive my ex-girlfriend and by taking responsibility of how I also had contributed to our relationship problems helped me to gain the needed confidence to realize that I do have what it takes to create a better relationship for me in the future.

    I think that by continuing to the best of your abilities to fulfill your own life and at the same time help make him feel successful in making you happy will help him gain his confidence and see that he does make a difference and have what it takes to have a great relationship. Good luck to you both!

    1. 9.1

      No one makes their SO cheat. That’s a guilt trip she took you on to justify her actions. Oh you didn’t tell her you loved her enough, or bought her flowers enough, or took her out enough? Come on man… If she didn’t like that stuff, she could have left you but she didn’t. Why? Because she loves you? Sure! I mean, who doesn’t cheat on their loved ones?! You found an attention sloot, not that hard to do this day and age. But if there’s one thing sloots are gonna do, it’s sloot around. I feel for ya. I’d hate to have to swallow my pride every time I looked at my girl.

      1. 9.1.1

        I think she already left him…

    2. 9.2
      just a girl

      Thank you for pointing out that there are 2 sides to every story.   People don’t cheat unless something is missing terribly.   Thrilled you stepped up to forgive her and you.   Happy future!


      1. 9.2.1

        You are wrong. I know some women who cheat when when they are happy.

  10. 10

    16 years and he’s still bitter? I realize that being cheated on is horrible, but I wonder how much more to the story there is.

    If he’s 42, that means he was 26 when he divorced. For how long was he married? And what were the circumstances? Was he traveling a lot for work and didn’t attend to his wife’s emotional needs? or was she a total wacko? Also, what was his relationship experience since his divorce?

    We all have baggage, but those who are successful in moving on are able to deal with it. My friends’ husband was married one before and his wife cheated on him. It took him a few years to get over it, an in the process learned about what he could have done better. Had he not gone through this he wouldn’t have been ready to date my friend. Now they’re happily married w kids.

    Your bf has to accept what happened in order to move on. And based on what you’re telling me, it doesn’t sound as if he has. And at 42, if he hasn’t learned how to deal w this, I doubt he ever will. And your staying w him won’t change that.

  11. 11

    I agree with Steve #2 He needs profesional help. Based upon what you’ve written,Vicki, it seems to me that there’s never been any sort of closure or emotional divorce. I can sepculate as to why, but that’s unimportant. The question remains is he willing to make the changes he needs to make in order to have a future with you? Honey # 3 made an excellent point. You’ve shown your concern for him, but the simple fact of the matter is he has to want to make those changes that are necessary for a healthy relationship. You can’t make change or want to change that has to come from within him and him alone. Change is hard and can be scary, especially when it comes to trust issues. None of us like being hurt, so it may be something he’s not willing to do as he hasn’t made an effort yet. It seems to me that you have to decide whether or not you can accept him as he is now and whether or not you’ll be happy or content with that. You can’t depend on him to change because he may not want to. Dysis #8 said it best…”I’m great enough for for him to get over it…And if he can’t, Im just gonna have to move on”

  12. 12

    I agree with many of the thoughts here. If he hasn’t been able to heal during all those years, then he needs professional help. I doubt that he will choose that route, unless he doesn’t want to lose you. It’s comforting for him to hold on to his security of distrust because then he doesn’t have to open himself up to the possibility of future pain and rejection, nor does he have to point the compass at himself to see where he may have played a part in her betrayal.

    It’s possible that you’re the first woman he has seriously considered since his divorce; thus challenging his trust issue. Three months may be too soon for him. Building trust takes time. It’s a shame how a lifetime of trust can crumble in a matter of seconds.

    That said, at some point ~ and I’d say sooner than later, given your developing feelings ~ you have to ask yourself, “If he doesn’t change, can I continue to live with this, accept him as he is, and be willing to lose a piece of myself in the process?” You already know the answer. All you can do is be the trusting person you are, and leave the rest up to him. And if you think you can live without his trust, your relationship will not last because every warrior gets weary. True love can only deepen and grow when there is trust.

    1. 12.1

      It’s also possible that he can’t make sense of her myriad of reasons for the betrayal so he feels very vulnerable trusting another woman because he realizes that he can’t control another person’s decisions.

      In my former marriage, my ex-husband cheated, I became very hyper-vigilant for several years trying to “be better” so he wouldn’t cheat again and…he cheated again. I find that trying to understand what happened so I could make it not happen again with him or someone else is maddening. It just made me feel like I have some kind of vague irreversible flaw that I can’t quite put my finger on. I always wanted the reasons for the betrayal to be something simple and concrete so that I could point the compass at myself and change. That way no one would ever hurt me again, but as my therapist said “there are no guarantees.”

      I have read from other people who are cheated on that they didn’t heal and move on until they STOPPED blaming themselves for their ex’s betrayal.

      On the flip side, my needs were neglected and I felt like I had a lot of reasons to turn to another man for comfort during my marriage, but I chose not to betray my ex-husband. If your SO never cheated in any of his relationships, that is something to be proud of and should let him know that some people have it in them to not cheat.

  13. 13

    To clarify what might sound conflicting, 😉 16 years is long enough for him to heal, assuming she’s not the first woman to challenge his trust issue which is likely the case.

    1. 13.1
      A random 40 year old single guy

      4 years was long enough.

      It’s more than likely he keeps stubbornly reviewing and rehearsing the same old worst case scenarios in his head.   This keeps strengthening the very synapses he needs to shut down.

  14. 14

    I’m also curious as to what his romantic life has been the last 16 yrs. between ages 26 and 42. Did he not date? Or relegate himself to casual relationships only? Did he alienate a number of potential partners with his mistrust of them and women in general?

    Only 3 months into dating you are likely still in the “new” infatuation stage. Having to continually “prove” yourself to someone who presumes guilty by gender is going to become increasingly tiresome as the newness of this relationship wears off. I don’t think there is anything you can do to help him “get over” his feelings resulting from the past. How do you know he even wants to? Perhaps holding onto mistrust has become a comfort zone to him. A way of keeping lovers at a measured distance. Of keeping them on edge with the “proving” thing. Of excusing himself from making a commitment to any woman. A bit convenient if you think about that way.

    He’d have to actually want to get over his trust issues and do something like therapy in order for the two of you to move on from his past. How likely do you think that is? 3 months may be too early for you to push for something like that. After 6 months together though, you need to seriously consider what a future with this guy is going to look like and discuss it with him accordingly.

  15. 15

    It’s a shame that at some point as we get older we will all have some baggage that makes us see things in a way we never thought we would. I have been in the position where I have to pay the price for another’s bad choices but the bottom line is we must make a conscious decision as to whether that person is worth the extra time and patience or not. If not then cut your emotional ties and head for the door.

  16. 16

    My boyfriend was cheated on by his first love after 5 years of dating, the fact that she married this other guy didn’t help his road to recovery. He can’t see it from her perspective but I can’t help thinking, if she moved on with this guy so quickly perhaps they weren’t made for each other?
    We’ve had lots of talks about starting with a blank slate and I’ve always shown myself to be open and trustworthy such as letting him know where I am and what I’ve been up to. Its little things like this that prove yourself and help them to realize that they have nothing to fear with you. Good luck.

  17. 17

    I’m reading this post as a guy who has been cheated on and is recently starting a new relationship with a girl who seems completely awesome so far. I’ve NEVER been a jealous guy because I so “blindly” trusted the person I was with. Long story short, I was with my girlfriend for 6 years before I asked her to marry me. And after six months  of marriage  (7 years of being together), she told me she didn’t love me anymore. And I found out the hard way (through piecing things together by talking with her mom) that she had been lying to me and hanging out with the guy that she is still currently with while we were still married. When I confronted her about hanging out with this guy, she told me she wanted a divorce. This was on a tuesday, and that following weekend, she went on a “weekend getaway” with this guy. It was probably the worst week of my life – literally. I have never once blamed her, or even been mad at her, for falling out of love with me. It’s just the lying and completely defying my trust that is hard to get over.
    Now I also realize that I wasn’t a perfect guy, but at the same time, who is? And she definitely had her flaws too. But we were crazy about each other. Or so I thought.  And after having a seven year relationship go bad out of nowhere, I find myself continuously thinking how can anyone know for sure that they aren’t going to get hurt? There is simply no way to know for sure. Which is the scary part. At any time, the person you are with could find someone better and decided to go with them. It’s just a tough hurdle to get over.
    So I completely understand where this guy is coming from. We have been taught to not fully trust in women and it’s hard going against that. Really hard. I also don’t like how other people have been so quick to assume that it was the guys fault that the woman cheated. That’s simply not always the case. Both my wife and I constantly reminded each other how good the other person was for us. Especially when we looked at major flaws in other couple’s relationships. Everything looked really good for the future. I truly believe it was just simply a case of she found a bigger fish in the pond and went for it.
    Now I know my post was long and ultimately didn’t do much, but I just wanted to contribute my point of view from the “guy who’s having trust issues” perspective. (This is the first time I’ve ever posted to something like this too. I just googled how I felt, this page came up and I thought by reading it I would get some answers.)

    1. 17.1

      Thanks for sharing your story Trevor.   I’ve never being cheat on,   but I’ve always dreamed of having a successful marriage. It’s so hard to even dream of a having a successful marriage nowadays when you hear about stories like this. I just want to stay positive on life and believe that there are people out there who are faithful to their spouses until the end. Apparently marriage is not what it used to be any more… Which makes me so sad.

  18. 18

    a common thread in the responses is “he needs to get over it”
    be ing cheated on, especially in a relationship that has progressed
    to the level of marriage, does more psychological harm than many
    of you may realize. would you expect a rape victim to “get over it”
    and move on? acknowledging and supporting the emotional needs
    of ur partner is requires for any relationship and you have to be
    willing to make changes in yourself and how you act   to be able
    to grow with them. telling him he has to trust because its been 16
    years is not constructive. as with any victim of psychological
    trauma, you have to become aware of what triggers there anxiety
    and avoid these catalysts.   communication, compassion,
    acceptance and  understanding need to be part of the relationship.
    weather you like it or not, if you want to remain with this person,
    you have to be careful of how you act and what you say. the  
    question that should be asked is, are you strong enough to be
    with them and do you have faith that you can understand and  
    accept what they have been through, survived, and grow with
    them. bottom line is, you have to be as strong as they have had
    to be.

  19. 19

    Aw, He needs to forget about the past and  realize  that you will never do what his ex has done to him. It usually takes a little while for someone to be able to trust again, but 16 years is a bit ridiculous :L lol. Well it sounds like his ex has left the poor guy in pieces, keep telling him that you want to be with him for a very long time and that you would never do such a thing as be unfaithful to him or leave him. He will  eventually  start gaining your trust and I wish you all the luck 🙂 xxx

  20. 20

    nbdy wakes up ne day and says” i think i will cheat n my spouse.sometimes people are neglected r taken forgranted..sometimes they were silently unhappy…i have been lied t and cheated n and every day i try my hardest t start new with wh ever i might be with…withut judgement…until they give me a reasn itherwise

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